Compositions and methods of preparation thereof

Abstract

Described herein are methods of preparing compounds derived from triglycerides or condensation polymers such as polyesters and/or polyamides. The methods may include subjecting triglyceride or condensation polymer containing matter to mechanical processing in the presence of a nucleophile.

What is claimed is: 
     
       1. A method for depolymerizing polyester-containing compounds into constituent oligomer and/or monomers, the method comprising:
 contacting a polyester-containing compound with a nucleophile to form a first mixture, wherein the polyester-containing compound is a triglyceride, and the nucleophile is a hydroxide selected from potassium hydroxide, sodium hydroxide, barium hydroxide, cesium hydroxide, and calcium hydroxide; 
 mechanically processing the first mixture to decompose at least a portion of the polyester-containing compound to yield a second mixture comprising the constituent oligomer and/or monomers of the polyester-containing compound; and 
 isolating at least a portion of the constituent oligomer and/or monomers from the second mixture. 
 
     
     
       2. The method of  claim 1 , wherein the mechanical processing comprises grinding the first mixture. 
     
     
       3. The method of  claim 2 , wherein grinding the first mixture comprises ball milling. 
     
     
       4. The method of  claim 2 , wherein grinding the first mixture comprises planetary ball milling, and the first mixture is milled at a spinning frequency of about 1 rpm to about 1000 rpm. 
     
     
       5. The method of  claim 1 , wherein the mechanical processing comprises agitating the first mixture. 
     
     
       6. The method of  claim 1 , wherein the mechanical processing reduces the particle size of at least a portion of the second mixture to a mean particle size of less than about 1000 microns. 
     
     
       7. The method of  claim 1 , wherein isolating at least a portion of the constituent monomers from the second mixture comprises treating the second mixture with an acid. 
     
     
       8. The method of  claim 7 , wherein the acid is an inorganic acid. 
     
     
       9. The method of  claim 7 , wherein the acid is selected from hydrochloric acid, phosphoric acid, and sulfuric acid. 
     
     
       10. The method of  claim 7 , wherein treating the second mixture with an acid forms a solution having a pH less than or equal to 5. 
     
     
       11. The method of  claim 1 , wherein the constituent monomers comprise at least one compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10  are each independently —H, —OR 13 , —NR 13 R 14 , —SR 13 , halogen, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 13 , —NR 13 R 14 , —SR 13 , or halogen; 
 R 13  and R 14  are each independently —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, or —C 2 -C 6  alkynyl, 
 R 12  is —OH, —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 13 , —NR 13 R 14 , —SR 13 , halogen, —COOH, or —COOR 11 ; 
 m, n, and o are each independently an integer in the range of 0 to 30; and 
 the sum of m, n, and o is 0 to 30. 
 
       
     
     
       12. The method of  claim 1 , wherein the constituent monomers comprise at least one compound of Formula II: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 , R 2 , R 4 , and R 5  are each independently —H, —OR 11 , —NR 11 R 12 , —SR 11 , halogen, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 11 , —NR 11 R 12 , —SR 11 , or halogen; 
 R 11  and R 12  are each independently —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, or —C 2 -C 6  alkynyl; 
 the symbol   represents an optionally single or cis or trans double bond; 
 R 3  is —OH and R 3′  is selected from —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, and aryl when   between R 3  and R 3′  is a single bond, and R 3  and R 3′  are absent when   between R 3  and R 3′  represents a double bond; 
 R 6  is —OH and R 6′  is selected from —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, and —C 6 -C 10  aryl when   between R 6  and R 6′  is a single bond, and R 6  and R 6′  are absent when   between R 6  and R 6′  represents a double bond; 
 n is an integer in the range of 0 to 11; 
 m is an integer in the range of 0 to 25; and 
 the sum of m and n is 0 to 25. 
 
       
     
     
       13. The method of  claim 1 , wherein the constituent monomers comprise at least one compound of Formula III: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 13  are each independently, at each occurrence, —H, —OR 14 —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; 
 R 3 , R 4 , R 7 , and R 8  are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkenyl, —C 2 -C 6  alkynyl, —C 3 -C 7  cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen, wherein:
 R 3  and R 4  can combine with the carbon atoms to which they are attached to form a C 3 -C 6  cycloalkyl, a C 4 -C 6  cycloalkenyl, or 3- to 6-membered ring heterocycle, and/or 
 R 7  and R 8  can combine with the carbon atoms to which they are attached to form a C 3 -C 6  cycloalkyl, a C 4 -C 6  cycloalkenyl, or 3- to 6-membered ring heterocycle; 
 
 R 14  and R 15  are each independently, at each occurrence, —H, —C 1 -C 6  alkyl, —C 2 -C 6  alkenyl, or —C 2 -C 6  alkynyl; 
 the symbol   represents a single bond or a cis or trans double bond; 
 the symbol   represents a cis or trans double bond; 
 n is 0, 1, 2, 3, 4, 5, 6, 7, or 8; 
 m is 0, 1, 2, or 3; 
 q is 0, 1, 2, 3, 4, or 5; and 
 r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.